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Search results; Over 1,000 homes in Dalton

Top guest favourite
Home in Dalton
Brooksong, the perfect Berkshires getaway
5 bedrooms, 7 beds, 2.5 private bathrooms
22–27 Sept
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4.93 out of 5 average rating, 212 reviews
Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 bathrooms
14–19 Oct
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Dalton
Willowbrook: A Sun Filled, Mid-century Modern Home
7 bedrooms, 8 beds, 4.5 bathrooms
20–25 Sept
4.78 out of 5 average rating, 113 reviews
Top guest favourite
Guest suite in Dalton
Berkshires getaway: nature, culture & relaxation
1 bed, 1 bathroom
15–20 Sept
4.99 out of 5 average rating, 80 reviews
Guest favourite
Flat in Dalton
1843 House - Bright and Airy 5 Rooms (2 Bedrooms)
2 bedrooms, 3 beds, 1 bathroom
31 Oct – 5 Nov
4.91 out of 5 average rating, 22 reviews
Guest favourite
Home in Lanesborough
Cozy Cottage in Berkshires: Minutes to Jiminy Peak
4 bedrooms, 5 beds, 1.5 bathrooms
15–20 Sept
4.97 out of 5 average rating, 79 reviews
Top guest favourite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds, 4 bathrooms
20–25 Sept
4.94 out of 5 average rating, 47 reviews
Guest favourite
Home in Dalton
Cleveland House - renovated Berkshires' gem.
6 bedrooms, 8 beds, 3 bathrooms
1–6 Aug
4.99 out of 5 average rating, 181 reviews
Guest favourite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
3 bedrooms, 4 beds, 1 bathroom
28 Oct – 2 Nov
4.93 out of 5 average rating, 135 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 76 reviews
Top guest favourite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 bedrooms, 5 beds, 2 bathrooms
17–22 Sept
4.95 out of 5 average rating, 75 reviews
Guest favourite
Cottage in Lanesborough
Lakefront Cottage | Private Dock, Kayaks & Firepit
2 bedrooms, 6 beds, 1 bathroom
5–10 Oct
4.79 out of 5 average rating, 14 reviews
Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
4.84 out of 5 average rating, 194 reviews
Guest favourite
Cabin in Hinsdale
Relaxing Berkshire cabin on Lake Ashmere
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 50 reviews
Guest favourite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.97 out of 5 average rating, 130 reviews
Guest favourite
Home in Pittsfield
Berkshire Views
6 bedrooms, 7 beds, 4 bathrooms
11–16 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Pittsfield
The Reel Retreat | Theatre & Firepit • Game Room
4 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 46 reviews